How much will Obama’s being black matter in the end? In, say, 20 years, will it be a major or minor aspect of his presidency and, to the extent that it will matter, in what specific way will it matter most?

In 1970, William F. Buckley Jr. wrote an essay for Look magazine called �Why We Need a Black President in 1980.� It took 28 years longer than he recommended, a postponement that allowed Ronald Reagan to be elected in 1980, but Barack Obama consummated Buckley’s wish in the new century.

A black president, WFB argued, would vindicate American idealism, providing blacks the �reassurance� that their equality included access to the highest office in the land and, at the same time, providing �a considerable tonic for the white soul� by dispelling charges of hypocrisy.

Obama’s presidency has done some of that admirable work, which may prove his most enduring achievement. Clare Boothe Luce claimed that every presidency can be reduced to a single sentence with an active verb, e.g., �Lincoln freed the slaves,� �Nixon resigned.� It is hard to find an active verb for Obama. Which is why �Obama was the first black president� bids fair to be his epitaph.

But his administration has not come as close to transcending race as most Americans would have liked and expected. Obama introduced himself to America in 2004, and ran in 2008, as a uniter not a divider. That’s why Reverend Jeremiah Wright’s denunciations of inexpiable American racism (�God damn America!�) proved so disruptive. Now, after his reelection, one sees Obama speaking at events sponsored by, and on behalf of causes dear to, the race-hustling Reverend Al Sharpton. When historians reopen these questions, they will discover why it was difficult for Obama to stick to the high road: He never accepted, though he often borrowed, Martin Luther King Jr.’s view of the non-racist, indeed anti-racist quality of America’s founding principles.

Will future historians blame Obama for not getting more done in a climate of Republican obstructionism, or will he be given a pass for it? More generally, to what degree will his presidency be seen as �transformative� (the word he used to describe the Reagan administration)?

Divided government has been the norm in America since 1968. Whether to blame it on the Republicans or the Democrats is beside the point, since it takes two to deadlock. What is interesting is how and why Obama managed to break through it for two years.

Obama set out to transform American politics, and he half-succeeded. First, he had to persuade liberals to believe in liberalism again�to believe in the possibility of broad, deep, and rapid political change, engineered by an activist federal government, led by a visionary prophet-president. No more Clintonian small ball. That was the �hope� part. Second came the �change�: He had to prove he could pull it off, could turn the renewed dreams into reality. In the first half of his first term, he broke through the left-right stalemate and won passage of the stimulus bill, Dodd-Frank, and above all the Affordable Care Act. As he boasted to Steve Kroft in 2011 on CBS’s 60 Minutes, �I would put our legislative � accomplishments in our first two years against any president�with the possible exception of Johnson, FDR, and Lincoln �� The �possible exception,� mind you.

But those were the presidents to whom he was comparing himself. This was no timid, pragmatic Democrat eager to nudge America two degrees to the center left. Obama tried to restore liberalism to its exalted position as America’s governing public philosophy; and though it is easier for liberal historians to deny his ambition than to admit his failure, they have to reckon with both.

For, of course, the transformation fizzled. Political breakthrough was followed not by electoral breakthrough but by something closer to repudiation: the populist, right-wing fury of 2010 and its second wave in 2014. The Reagan Revolution’s own legacy, the deep suspicion of liberal government, had not been overthrown after all. Divided government came back with a vengeance.

Still, Obama’s political reversals forecast renewed political stalemate more surely than they did conservative triumphs. And historians will note that so long as Obamacare lives, there is hope for a more transformative legacy.

In assessing Obama’s historical legacy, what do you believe will be the aspect of his presidency that is currently least understood or misunderstood? In other words, for better or worse, what single thing looks smallest now but will matter most to future historians?

Obama’s presidency brought American liberalism to the point of imperial overreach. The passage of Obamacare, the kind of comprehensive national health insurance liberals had lusted after for a century, marked liberalism’s apogee. For the president, it was all basically downhill from there.

The manner of Obamacare’s passage told the story�a party-line vote, reeking of special-interest side deals, on an unpopular, indigestible, multi-thousand-page love letter to bureaucracy, crudely packaged as a reconciliation bill to avoid filibuster, and falsely sold, in read-my-lips promises that would come back to haunt Obama, as the most conservative possible approach to health-care reform. This was liberalism à outrance�its last desperate surge to win at any cost what it could no longer even imagine winning honestly and on the merits.

Is this the seed from which a purer, stronger, more social-democratic American liberalism will now spring, as its defenders hope? I doubt history will confirm that.

This costly, and probably temporary, victory seems more likely to mark the beginning of a crisis in which liberals will be forced to confront the dread thought�and worse, the dawning political reality�that they are not on the right side, which means, for liberals, the winning side, of history.

If I’m right, future historians will reckon the Obama administration’s hubris to be its least understood and most consequential aspect.

Will future historians conclude that Obama weakened or strengthened the office of the president? Will the policies he enacted without congressional cooperation represent a strategic victory or a dangerous escalation of executive power?

In domestic politics, the go-it-alone approach signals presidential weakness more often than it does strength. What kind of �imperial president� boasts of having a pen and a phone � and being prepared to use them? There are very few executive actions Obama can take that the Republican House and Senate, responsibly asserting their legislative powers, could not counter or cabin. The courts, avid readers of the election returns, may be tempted to intervene against a weak president, too. History will note constitutional fireworks but no blood.

Assuming no dramatic shift in world events between now and 2016, which parts of Obama’s foreign-policy tenure will be judged most positively and which most poorly? Overall, how will his actions abroad be judged against his recent predecessors’?

Caught between the �responsibility to protect� and an aversion to war and warlike actions, the Obama administration’s foreign policy has been whipsawed by competing liberal imperatives. Should the U.S. wage war to prevent genocide or shun war because it is akin to genocide�especially when the war in question would be waged by an America with copious blood on its historical hands?

The public, at least until 2013 or so, had thought more highly of Obama’s foreign policy than had the experts. Obama had reined in the George W. Bush administration’s enthusiasm for democratization, winding down the open-ended occupations of Iraq and Afghanistan. So far as it went, that was popular and mostly sensible. But the competing liberal imperatives tended to cancel each other out, leaving no room for an �Obama doctrine� as such; what remained was a practical attitude, �Don’t do stupid shit.�

Defining �stupid� proved difficult, however, particularly given Obama’s impatience with, and occasional condemnation of, geopolitics. Whether a good idea or not, the pivot to Asia could never be a serious strategic doctrine so long as the Navy was ordered to shrink dramatically and missile defense remained a marginal concern. In an age of globalized banking, economic sanctions proved more effective than their history might have suggested. Vladimir Putin derided Obama’s (and NATO’s) lack of geopolitical seriousness but couldn’t laugh off the economic squeeze they applied.

Obama’s foreign policy commenced with soaring but uncertain rhetoric. When the lighter elements boiled away, what was left was a coping strategy, which proved to be more about coping than about strategy. Historians will praise Obama’s foreign policy as better than Bush’s, which it was not, but that will be their own way of coping with the long, disappointing post-Reagan era of American statecraft.

Will the Obama years come to be seen as a major realignment in Democratic politics? As a historian, how would you predict the longevity of his coalition?

Under Obama, the Obama coalition deteriorated; his reelection was a shadow of his 2008 victory. Without Obama, the Obama coalition will deteriorate precipitously. His absence from the ballot is not the only or perhaps even the major problem. The �emerging Democratic majority� will likely not emerge because liberalism faces latent problems, beginning with the fact that it will have increasing difficulty, in Bill Voegeli’s phrase, making payroll. To pay for Social Security, Medicare, Medicaid, and now Obamacare will eventually require enormous middle-class tax increases. Walter Mondale was the last Democratic presidential candidate to propose such levies, and his fate taught his party to stick to Peter Pan economics. Obama feigned interest in leaving Neverland a few times but, through 2014, continued to govern in denial of the unpleasant, and worsening, fiscal realities.

Complicating life for liberals is the bright light the Obama administration shined on another facet of big government: its incompetence. With the spectacularly inept rollout of Obamacare, not to mention ancillary scandals at Veterans Affairs and the IRS, the hope of demonstrating once and for all the ethical and intellectual superiority of modern, liberal government suffered an unforgettable setback. The authoritative (and need I add, authoritarian) obscurity of the administrative state had been pierced. This issue, the increasingly visible incoherence, disability, and corruption of the state apparatus itself, will loom large in the next two decades, alienating millions of voters along the way.

Will future historians concur with the administration’s own narrative of having saved the country from another Great Depression? Or will Obama’s economic legacy be seen as a lackluster performance or, worse, a failed attempt to reform the U.S. economy in any meaningful way?

Here is another reason why liberalism’s claim to know how to run things will be increasingly disbelieved. People have noticed that the Great Recession was not followed by a Great Recovery. Obama himself laughs now at the idea of �shovel-ready� jobs. Thanks to Republican �obstructionism,� the Federal Reserve’s generosity, and the inherent strength of the American economy, a good fracking recovery finally emerged in 2014. As he should, Obama will get very little credit for it.

What single action could Obama realistically do before the end of his term that would make the biggest positive difference to his historical legacy?

Embrace the gutting, er, reform, of Obamacare.

What will be seen as Obama’s single most significant accomplishment?

The passage of Obamacare is the highlight reel. If the Court strikes it down, or if the program is repealed, then Obama’s reputation is toast.

Will Obama’s reputation have improved or declined in 20 years?

His public reputation will decline to middling levels, a step or two above Jimmy Carter, though this standing could be influenced by Obama’s long post-presidential career. Among historians, who are overwhelmingly liberal, Obama will rank a step or two above or below JFK.

Which of Obama’s speeches and phrases will be the most enduring?

Despite his reputation, Obama lacks eloquence and his speeches, with a handful of early exceptions, are workaday. He has said nothing memorable.

In which presidential mode was Obama the most effective: orator, legislator, commander-in-chief, consoler of the nation, or some other mode?

Orator, obviously, though our standards have sunk, obviously. Compare Obama’s speeches to Woodrow Wilson’s if you’d like to become reacquainted with liberal eloquence.

Will the image of Obama overshadow his accomplishments, in the manner of JFK?

Yes, but not by as much as JFK’s did.

Who will be seen as the most consequential member of his Cabinet or senior staff?

Eric Holder, which shows what a lackluster �team of rivals� filled Obama’s cabinet.

Which will prove to be more significant: the reduction of troops on the ground or the increase in the use of military drones?

Troop reductions.

What will be the most lasting image of the Obama presidency?

The �Hope� poster from Obama’s 2008 campaign.